CA2032988A1 - Process for preparing 1-phenylimidazoline-2,5-dione - Google Patents

Process for preparing 1-phenylimidazoline-2,5-dione

Info

Publication number
CA2032988A1
CA2032988A1 CA002032988A CA2032988A CA2032988A1 CA 2032988 A1 CA2032988 A1 CA 2032988A1 CA 002032988 A CA002032988 A CA 002032988A CA 2032988 A CA2032988 A CA 2032988A CA 2032988 A1 CA2032988 A1 CA 2032988A1
Authority
CA
Canada
Prior art keywords
formula
image
denote
alkyl
product
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002032988A
Other languages
French (fr)
Other versions
CA2032988C (en
Inventor
Patrick Seuron
Daniel Varraillon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aventis Pharma SA
Original Assignee
Patrick Seuron
Daniel Varraillon
Roussel Uclaf
Roussel-Uclaf
Hoechst Marion Roussel
Aventis Pharma S.A.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Patrick Seuron, Daniel Varraillon, Roussel Uclaf, Roussel-Uclaf, Hoechst Marion Roussel, Aventis Pharma S.A. filed Critical Patrick Seuron
Publication of CA2032988A1 publication Critical patent/CA2032988A1/en
Application granted granted Critical
Publication of CA2032988C publication Critical patent/CA2032988C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin

Abstract

New process for the preparation of the products of formula (I): <IMAGE> in which:   R1, R2 and R3, which are identical or different, denote H, alkyl, alkenyl, alkynyl, alkyloxy, alkenyloxy, alkynyloxy, phenyl, phenoxy, nitro, trifluoromethyl, acyl or esterified carboxyl,   R4, R5 and R6, which are identical or different, denote H or alkyl, characterised in that the product of formula (II): <IMAGE> in which R1, R2 and R3 have the meaning shown above and Hal denotes a halogen atom, is reacted with the product of formula (III): <IMAGE> in which R4, R5 and R6 have the meaning shown above, the reaction taking place in the presence of a catalyst, optionally of a solvent.
CA002032988A 1989-12-22 1990-12-21 Process for preparing 1-phenylimidazoline-2,5-dione Expired - Lifetime CA2032988C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8917046 1989-12-22
FR8917046A FR2656302B1 (en) 1989-12-22 1989-12-22 NEW PROCESS FOR THE PREPARATION OF ANANDRON AND ANANDRON DERIVATIVES.

Publications (2)

Publication Number Publication Date
CA2032988A1 true CA2032988A1 (en) 1991-06-23
CA2032988C CA2032988C (en) 2003-04-29

Family

ID=9388859

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002032988A Expired - Lifetime CA2032988C (en) 1989-12-22 1990-12-21 Process for preparing 1-phenylimidazoline-2,5-dione

Country Status (24)

Country Link
US (1) US5166358A (en)
EP (1) EP0436426B1 (en)
JP (1) JP2836041B2 (en)
KR (1) KR0173307B1 (en)
CN (1) CN1048011C (en)
AT (1) ATE107289T1 (en)
AU (1) AU628699B2 (en)
CA (1) CA2032988C (en)
CZ (1) CZ281655B6 (en)
DE (1) DE69009964T2 (en)
DK (1) DK0436426T3 (en)
ES (1) ES2055382T3 (en)
FI (1) FI103203B1 (en)
FR (1) FR2656302B1 (en)
HU (1) HU207301B (en)
IE (1) IE65510B1 (en)
IL (1) IL96696A (en)
NZ (1) NZ236621A (en)
PL (1) PL164694B1 (en)
PT (1) PT96313B (en)
RU (1) RU1836356C (en)
SK (1) SK656790A3 (en)
UA (1) UA27220C2 (en)
ZA (1) ZA909648B (en)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5411981A (en) * 1991-01-09 1995-05-02 Roussel Uclaf Phenylimidazolidines having antiandrogenic activity
FR2693461B1 (en) * 1992-07-08 1994-09-02 Roussel Uclaf New substituted phenylimidazolidines, process for their preparation, their use as medicaments and the pharmaceutical compositions containing them.
FR2694290B1 (en) * 1992-07-08 1994-09-02 Roussel Uclaf New phenylimidazolidines which may be substituted, their preparation process, their use as medicaments and the pharmaceutical compositions containing them.
US5656651A (en) * 1995-06-16 1997-08-12 Biophysica Inc. Androgenic directed compositions
FR2741346B1 (en) * 1995-11-16 1997-12-19 Roussel Uclaf NEW PROCESS FOR THE PREPARATION OF PHENYLIMIDAZOLIDINE DERIVATIVES
FR2741342B1 (en) * 1995-11-22 1998-02-06 Roussel Uclaf NOVEL FLUORINATED OR HYDROXYLATED PHENYLIMIDAZOLIDINES, METHOD, PREPARATION MEDIA, APPLICATION AS MEDICAMENTS, NEW USE AND PHARMACEUTICAL COMPOSITIONS
JPH1072446A (en) * 1996-06-24 1998-03-17 Sumitomo Chem Co Ltd Production of 1-substituted hydantoins
AU8821301A (en) * 2000-06-28 2002-01-08 Bristol Myers Squibb Co Selective androgen receptor modulators and methods for their identification, design and use
EP1854798A3 (en) 2000-09-19 2007-11-28 Bristol-Myers Squibb Company Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function
US20040087548A1 (en) 2001-02-27 2004-05-06 Salvati Mark E. Fused cyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function
EP1709193B1 (en) * 2003-12-19 2011-03-16 The Regents of The University of California Methods and materials for assessing prostate cancer therapies
WO2005099693A2 (en) * 2004-02-24 2005-10-27 The Regents Of The University Of California Methods and materials for assessing prostate cancer therapies and compounds
US7709517B2 (en) 2005-05-13 2010-05-04 The Regents Of The University Of California Diarylhydantoin compounds
US8445507B2 (en) 2006-03-27 2013-05-21 The Regents Of The University Of California Androgen receptor modulator for the treatment of prostate cancer and androgen receptor-associated diseases
NZ572374A (en) 2006-03-29 2011-12-22 Univ California Diarylthiohydantoin compounds
EP2620432A3 (en) 2007-10-26 2013-12-18 The Regents Of the University of California Diarylhydantoin compounds
CN103724322B (en) 2010-02-16 2017-05-03 亚拉冈制药公司 Androgen receptor modulators and uses thereof
UA117663C2 (en) 2012-09-26 2018-09-10 Арагон Фармасьютікалз, Інк. Anti-androgens for the treatment of non-metastatic castrate-resistant prostate cancer
JOP20200097A1 (en) 2013-01-15 2017-06-16 Aragon Pharmaceuticals Inc Androgen receptor modulator and uses thereof
TWI726969B (en) 2016-01-11 2021-05-11 比利時商健生藥品公司 Substituted thiohydantoin derivatives as androgen receptor antagonists
EP3697398A1 (en) 2017-10-16 2020-08-26 Aragon Pharmaceuticals, Inc. Anti-androgens for the treatment of non-metastatic castration-resistant prostate cancer

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH166004A (en) * 1934-06-06 1933-12-15 Chem Fab Vormals Sandoz Process for the preparation of a derivative of 5,5-phenylethylhydantoin.
US2490813A (en) * 1944-11-29 1949-12-13 Standard Oil Co Continuous process for making aryl amines
US2759002A (en) * 1954-03-24 1956-08-14 Abbott Lab 3-benzyl hydantoin and process
US3134663A (en) * 1957-07-23 1964-05-26 Geigy Chem Corp Herbicidal composition and method employing hydantoins
US3914311A (en) * 1973-06-15 1975-10-21 Du Pont Preparation of aromatic secondary and tertiary amines using a nickel complex catalyst
DE2414613A1 (en) * 1974-03-26 1975-10-16 Bayer Ag 1-ARYL-5-ALKYLIDEN-2,4-DIOXO-IMIDAZOLIDINE
FR2329276A1 (en) * 1975-10-29 1977-05-27 Roussel Uclaf NEW SUBSTITUTES IMIDAZOLIDINES, METHOD OF PREPARATION, APPLICATION AS A MEDICINAL PRODUCT AND COMPOSITIONS CONTAINING THEM
IL55774A (en) * 1977-10-28 1982-04-30 Sparamedica Ag Pharmaceutical compositions containing urea derivatives,certain such novel derivatives and their manufacture
GB1598166A (en) * 1978-05-23 1981-09-16 Lilly Industries Ltd 3,5-disubstituted hydantoin derivatives
US4764625A (en) * 1980-12-12 1988-08-16 Xerox Corporation Process for preparing arylamines
EP0091596B1 (en) * 1982-04-08 1991-09-11 Shell Internationale Researchmaatschappij B.V. Hydantoins, their preparation and application

Also Published As

Publication number Publication date
HU908416D0 (en) 1991-07-29
FR2656302A1 (en) 1991-06-28
RU1836356C (en) 1993-08-23
EP0436426A1 (en) 1991-07-10
EP0436426B1 (en) 1994-06-15
FI906366A (en) 1991-06-23
CN1048011C (en) 2000-01-05
PT96313B (en) 1998-06-30
ZA909648B (en) 1992-02-26
FR2656302B1 (en) 1992-05-07
UA27220C2 (en) 2000-08-15
CN1052666A (en) 1991-07-03
NZ236621A (en) 1992-04-28
CA2032988C (en) 2003-04-29
JPH04103573A (en) 1992-04-06
CZ281655B6 (en) 1996-12-11
FI103203B (en) 1999-05-14
PL288365A1 (en) 1991-09-09
AU628699B2 (en) 1992-09-17
CZ656790A3 (en) 1996-08-14
IE904142A1 (en) 1991-07-03
PT96313A (en) 1991-09-30
SK278447B6 (en) 1997-06-04
IE65510B1 (en) 1995-11-01
HU207301B (en) 1993-03-29
IL96696A0 (en) 1991-09-16
ATE107289T1 (en) 1994-07-15
JP2836041B2 (en) 1998-12-14
FI906366A0 (en) 1990-12-21
AU6826590A (en) 1991-06-27
SK656790A3 (en) 1997-06-04
FI103203B1 (en) 1999-05-14
IL96696A (en) 1995-08-31
PL164694B1 (en) 1994-09-30
KR0173307B1 (en) 1999-02-01
US5166358A (en) 1992-11-24
DE69009964T2 (en) 1994-10-13
DK0436426T3 (en) 1994-07-04
KR910011799A (en) 1991-08-07
DE69009964D1 (en) 1994-07-21
ES2055382T3 (en) 1994-08-16

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